Homes for Sale near Community Schoolhouse

/18
$634,500
- 3 Beds
- 2 Baths
- 1,448 Sq Ft
23 Bittersweet Ln, Chesterfield, NH 03466

Escape the day to day with this lovely waterfront Cape! Down your private deadend road, beside the hillside and quaint horse fence, awaits majesticviews to envelop you at this park-like setting on the Connecticut River. This primarily private 3-acre property has over 700’ of breathtaking scenery of riverfront with yourown beach area and rock jetty. Enter through your 2-Bay Garage with above

Mary M. Belle Isle EXP Realty

23 Bittersweet Ln, Chesterfield, NH 03466
/37
$499,000
- 3 Beds
- 2.5 Baths
- 2,024 Sq Ft
46 Poplar Commons, Dummerston, VT 05301

Nestled in the heart of Vermont, this charming Cape Cod-style home offers the perfect blend of country living and modern convenience. With 3 spacious bedrooms and 2.5 baths, it's designed for both comfort and functionality. The home boasts a large sunroom, perfect for enjoying Vermont's scenic beauty year-round, and a screened-in porch for those warm summer evenings. The outdoor deck provides an

Josh Greenwald Greenwald Realty Group

46 Poplar Commons, Dummerston, VT 05301
/60
$899,000
- 4 Beds
- 3.5 Baths
- 3,685 Sq Ft
155 Hillwinds N, Brattleboro, VT 05301

Situated in Brattleboro’s premier, rural neighborhood, this much-loved home is a masterclass in thoughtful design, meticulous construction, & refined living. A grand dbl-door foyer welcomes you into a soaring entry hall that flows seamlessly into a sunken, dbl-height ceiling LR - complete w/ granite-surround FP, custom blt-ins, & crowned by a dramatic balcony overlook. Light pours in from every

Dan Normandeau Berkley & Veller Greenwood Country

155 Hillwinds N, Brattleboro, VT 05301
/60
$695,000
- 3 Beds
- 2.5 Baths
- 2,315 Sq Ft
23 Meeting House Ln, Brattleboro, VT 05301

First Time on the Market – Premier Brattleboro Location!Nestled on one of the most desirable lots in one of Brattleboro’s finest neighborhoods, this well-maintained home is being offered for sale for the very first time! Custom-built by the current owner in 1970 with attention to detail, this spacious ranch offers comfort, functionality, and an impressive list of amenities.Perfect for

Bert Inman RE/MAX Town & Country

23 Meeting House Ln, Brattleboro, VT 05301
/27
$550,000
- 3 Beds
- 3 Baths
- 3,148 Sq Ft
672 E Orchard St, West Brattleboro, VT 05301

You can't beat this location, overlooking the Brattleboro Country Club golf course. This home was built circa 1919, and has many cool vintage features such as retro curved metal kitchen cabinets and baths. Generous rooms include a large living room with two field-stone fireplaces, a spacious family room. This is a 3 bedroom house with 3 full bathrooms, but it's really about how you configure

John Hatton Berkley & Veller Greenwood Country

672 E Orchard St, West Brattleboro, VT 05301
/60
$649,000
- 3 Beds
- 2 Baths
- 2,731 Sq Ft
49 Tyler St, Brattleboro, VT 05301

Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

Dan Normandeau Berkley & Veller Greenwood Country

49 Tyler St, Brattleboro, VT 05301
/51
$949,000
- 5 Beds
- 8 Baths
- 7,430 Sq Ft
925 Hinesburg Rd, Brattleboro, VT 05301

Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

Christine Lewis Brattleboro Area Realty

925 Hinesburg Rd, Brattleboro, VT 05301
/58
$859,000
- 3 Beds
- 3.5 Baths
- 3,212 Sq Ft
104 Juniper Ridge Rd, Brattleboro, VT 05301

Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has

Kristen Ziter Taylor Brattleboro Area Realty

104 Juniper Ridge Rd, Brattleboro, VT 05301
/2
$90,000
- 3 Beds
- 1 Bath
- 1,030 Sq Ft
93 Clark St, Brattleboro, VT 05301

An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please,

Christine Lewis Brattleboro Area Realty

93 Clark St, Brattleboro, VT 05301
/2
$89,000
- 4 Beds
- 3 Baths
- 2,108 Sq Ft
321 Williams St, Brattleboro, VT 05301

Great opportunity for starting or expanding your investment portfolio. Good rental income and affordable property. Nice location. Good parking for tenants and private porches. Minimal yard maintenance.

Susan Bellville Bellville Realty

321 Williams St, Brattleboro, VT 05301
/20
$249,000
- 6 Beds
- 2 Baths
- 1,968 Sq Ft
14-16 Valley St, Brattleboro, VT 05301

Perfectly situated on a quiet street close to downtown, stores, and schools, this well cared for duplex is a rare opportunity for owner-occupants or investors alike. Each spacious unit offers 3 bedrooms and 1 full bath, with a host of updates and energy-efficient upgrades throughout. Many recent upgrades include Solar panels, Finished and insulated attics, Partially finished basements, Gas

Claire Renaud Berkley & Veller Greenwood Country

14-16 Valley St, Brattleboro, VT 05301
/31
$349,900
- 3 Beds
- 1.5 Baths
- 1,073 Sq Ft
12 Breezy Knoll, Hinsdale, NH 03451

Charming 1930s Home Reimagined with Modern CraftsmanshipStep into the perfect blend of timeless character and modern convenience. Originally built in 1930, this beautifully reimagined home has been meticulously renovated from top to bottom—preserving the integrity of its historic craftsmanship while delivering all the updates today’s homeowners expect.No detail was overlooked, and no

Gerry Leo BHG Masiello Keene

12 Breezy Knoll, Hinsdale, NH 03451
/3
$150,000
- Land
- 4.30 Acres
- $34,884 per Acre
00 Orchard Rd, Chesterfield, NH 03443

A rare find in Chesterfield. 4+/- acres of mostly open land situated on a quiet country road. Long road frontage assures privacy and allows for your choice of driveway access. Located about 3 miles from Rt 9 and close to Chesterfield Elementary, this spot provides convenience to Keene, Brattleboro and Hinsdale. And is close to Spofford Lake and Pisgah Park.

Timothy Keating BHG Masiello Keene

00 Orchard Rd, Chesterfield, NH 03443
/16
$259,900
- Land
- 29 Acres
- $8,901 per Acre
1270 Melendy Hill Rd, Guilford, VT 05301

A rare find! This amazing land has long range views, privacy and close to everything! There is a right of way for egress, and will be perfect for an off grid tuck away cabin or primary. A small meadow is part of the 2 acre exemption for house site, just at the end of the existing drive...easy to get to and just the beginning of the land. Mostly Black Birch, Sugar Maple and Hemlock, there is

Christine Lewis Brattleboro Area Realty

1270 Melendy Hill Rd, Guilford, VT 05301
/56
$235,000
- 2 Beds
- 1.5 Baths
- 1,056 Sq Ft
67 Morningside Commons, Guilford, VT 05301

From the rhododendron, orange day lily and morning glories in front of this condo to the herb and flower garden in the rear and with everything in between, this condo speaks "lovely". Completely updated and immaculately maintained. Kitchen features stylish cabinets, Corian counter tops, all Whirlpool stainless steel appliances and a double oven. The hanging wrought iron pot holder and fruit

Sally Fegley BHG Masiello Brattleboro

67 Morningside Commons, Guilford, VT 05301
/10
$175,000
- Land
- 8 Acres
- $21,875 per Acre
680 W River Rd, Brattleboro, VT 05301

8 acres only 2 miles from Brattleboro situated across the road from the West River. Existing gated gravel driveway is in. Gravel on site and road roughed into a high plateau with designs for SIX 1-2 bedroom cottages. Topographical survey, septic design plans and other existing engineering are complete which make this an attractive option for someone looking to develop a parcel into a cottage

Chris Long BHG Masiello Brattleboro

680 W River Rd, Brattleboro, VT 05301
/18
$176,500
- 2 Beds
- 1 Bath
- 888 Sq Ft
15 Lynwood Dr, Brattleboro, VT 05301

This is absolutely NOT your ordinary Mobile Home! The original steel frame is the only remaining component of the mobile home. Completely rebuilt from the floor up with wood framing, windows, doors and insulation. This fully fenced leased lot has two sheds, a 1 car garage building with tons of storage and a workshop building with its own mini-split for heat and AC. The tastefully renovated

Chris Long BHG Masiello Brattleboro

15 Lynwood Dr, Brattleboro, VT 05301
/9
$80,250
- Land
- 3.10 Acres
- $25,887 per Acre
0 E Orchard St Unit 5047716, Brattleboro, VT 05301

A rare opportunity to purchase a lot in a highly desirable Brattleboro neighborhood. This 3+ acre wooded parcel features a mature pine forest with additional hardwoods intermixed, stonewalls and even a small stream. It's the location that makes this property unique. Just up the road from the Brattleboro Country Club on a quiet street that gives quick access to all that Brattleboro and the

Bill Hickok Berkley & Veller Greenwood Country

0 E Orchard St Unit 5047716, Brattleboro, VT 05301
/20
$270,000
- 3 Beds
- 2 Baths
- 2,062 Sq Ft
691 Brattleboro Rd, Hinsdale, NH 03451

Investor or house-hacker? This 2-unit multifamily delivers $24,000/year in gross income with both tenants paying $1,000/month. Utilities are split, meaning lower operating costs for you. At the $299,999 list price, this property offers a strong 8% cap rate with room to grow and value add potential.Upside opportunities abound: add a third unit, increase bedroom count in existing layouts,

Andrew Bosco Four Points Real Estate

691 Brattleboro Rd, Hinsdale, NH 03451
/11
$250,000
- Land
- 18 Acres
- $13,889 per Acre
0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

Christine Lewis Brattleboro Area Realty

0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
/12
$95,000
- 2 Beds
- 1 Bath
- 832 Sq Ft
48 Robbins St, Hinsdale, NH 03451

Thicket Hill Cooperation sits on a quiet hillside adjacent to the Connecticut River Reservoir. The town of Hinsdale is family friendly and perfect for nature lovers. It borders Connecticut River for 13 miles and boasts a popular Pisgah State Park access. From this home, it is only a five mile drive to Brattleboro and 22 miles to Keene. The home is a split level inside with an open concept

Jessie Carpenter Keller Williams Realty Metro-Keene

48 Robbins St, Hinsdale, NH 03451
/47
$299,000
- 3 Beds
- 1 Bath
- 1,222 Sq Ft
1082 W River Rd, Brattleboro, VT 05301

Welcome to 1082 West River Road — a peaceful, well-located gem just minutes from downtown Brattleboro. This charming home offers the perfect blend of convenience, outdoor space, and natural beauty. Set on a spacious lot with a large, open yard, there's room to garden, gather, or simply relax and enjoy the Vermont seasons. The private river access makes it easy to enjoy kayaking, swimming, or

Kate Barry EXP Realty

1082 W River Rd, Brattleboro, VT 05301
/60
$895,000
- 3 Beds
- 3 Baths
- 2,258 Sq Ft
266 Ursa Ridge Rd, Dummerston, VT 05301

This home is living art, tucked away at the end of the road of lovely homes & hundreds of acres ridgetop, yet only 10 minutes from downtown Brattleboro. Built by a craftsman this home is gracious & energy efficient. Building materials have been harvested from it's 51-1/2 acre woodland. Rooms are thoughtfully designed awash with natural light. Walk up the covered, stone walkway to enter the

Randi Ziter Brattleboro Area Realty

266 Ursa Ridge Rd, Dummerston, VT 05301
/18
$319,900
- 3 Beds
- 1 Bath
- 1,323 Sq Ft
164 Chestnut St, Brattleboro, VT 05301

Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with

Christine Lewis Brattleboro Area Realty

164 Chestnut St, Brattleboro, VT 05301
/42
$415,000
- 3 Beds
- 1.5 Baths
- 2,433 Sq Ft
183 Bear Hill Rd, Dummerston, VT 05301

Discover a hidden gem nestled deep in the woods—a rustic retreat that’s entirely off-grid and 100% solar powered. Perfect for nature lovers, creative spirits, or anyone seeking serenity and self-sufficiency.This one-of-a-kind property features a charming main house with a two-bedroom loft attached, currently used for short-term rentals. The main cabin exudes classic Adirondack charm with

Kate Barry EXP Realty

183 Bear Hill Rd, Dummerston, VT 05301
/5
$139,900
- Land
- 1.30 Acres
- $107,615 per Acre
00 Creamery Rd, Guilford, VT 05301

Just in time! Unbelievable! A high rolling meadow of your very own! Build the new home, the one you have been waiting for all your life, on this beautifully cared for sweet spot in the Vermont countryside community of Guilford. The boundaries are easy to find, one being right up to the edge of an old stone wall, the others marked with posts. Pick the high point and have a local view of old

Christine Lewis Brattleboro Area Realty

00 Creamery Rd, Guilford, VT 05301
/45
$1,100,000
- 3 Beds
- 2 Baths
- 2,210 Sq Ft
61 Orchard Rd, Chesterfield, NH 03443

Continue the legacy of owning the oldest home in Chesterfield with its rich history, bucolic setting of woods, fields, pond and orchard. Well maintained features include beamed ceilings, wide pine floors, slate roof and center chimney. The Custom kitchen has stainless steel appliances, cherry cabinetry and CaesarStone counters. White oak flooring was installed with programmable radiant

Timothy Keating BHG Masiello Keene

61 Orchard Rd, Chesterfield, NH 03443
/49
$925,000
- 4 Beds
- 2.5 Baths
- 4,116 Sq Ft
125 Stage Rd, West Chesterfield, NH 03466

19+ acres of ultimate privacy surround this spectacular home with timeless details and stunning views, offering a perfect blend of comfort & sophistication. The contractor/owner exquisitely built and maintained the property and thought of everything, starting with the welcoming foyer adorned with Spanish marble. The chef’s kitchen features granite counters, a downdraft gas stove, mesquite

Ben Prentice Keller Williams Realty Metro-Keene

125 Stage Rd, West Chesterfield, NH 03466
/23
$1,150,000
- 6,442 Sq Ft
69-71 Elliot St, Brattleboro, VT 05301

Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

Erica Reynolds Southern Vermont Realty Group

69-71 Elliot St, Brattleboro, VT 05301
/28
$200,000
- 3 Beds
- 1.5 Baths
- 1,531 Sq Ft
316 Putney Rd, Brattleboro, VT 05301

Convenient Location & Low Maintenance Living! Enjoy easy access to shopping, public transportation and waterfront with scenic trails. The backyard is just the right size for enjoying nature and a little fresh air. This charming home combines classic character with practical updates featuring a standing seam roof, vinyl windows and aluminum siding. Inside, the home radiates its original charm

Kerry Mulverhill Brattleboro Area Realty

316 Putney Rd, Brattleboro, VT 05301
/16
$488,875
- 5 Beds
- 4 Baths
- 3,064 Sq Ft
176 High St, Brattleboro, VT 05301

Unique opportunity to live very comfortably in the more than 1400 sq ft 1st floor apartment with private laundry, private covered porch and your own deck. The apartment has 2 plus bedrooms and 2 full bathrooms, eat in kitchen, dining room and living room. invest in your own home and have revenue from 2 apartments to help with costs. Apartment #2, on the 2nd floor, is a 1-2 bedroom unit which has

Susan Bellville Bellville Realty

176 High St, Brattleboro, VT 05301
/26
$725,000
- 18 Beds
- 8 Baths
- 4,932 Sq Ft
29 Canal St, Brattleboro, VT 05301

High cash flow 100% occupied 8 unit located in downtown Brattleboro. This property was recently renovated and is being listed at a 11% cap and an annual Net Operating Income estimated at north of ~$80K (12% cap without management fees). The property features an attractive mix of unit types and sizes including 4x rarely available oversized 3br, 2x2br and 2x1brA new owner can step into to

Michael Gilman 3GEN Real Estate Inc

29 Canal St, Brattleboro, VT 05301
/58
$650,000
- 4 Beds
- 2 Baths
- 3,090 Sq Ft
301 Maple St, Brattleboro, VT 05301

This is IT! Summer is here! The gardens are ablaze, the deck is perfect for the evening sip of something cool and there is open sky for sightings like the strawberry moon and shooting stars. Treat yourself to your own spa....the sweet spot is the oversized salt pool, surrounded by lush greenery for privacy and an apron for sunning. Add some of your own fun and you will stay at home,

Christine Lewis Brattleboro Area Realty

301 Maple St, Brattleboro, VT 05301
/29
$88,900
- Land
- 13 Acres
- $6,984 per Acre
0 Skyline Dr, Vernon, VT 05354

12+ Acres of Wooded Vermont Beauty This 12.73-acre parcel in peaceful Vernon, VT offers the ideal blend of privacy, natural beauty, and accessibility. With ample road frontage and electric available at the street, so much potential whether it be a vacation retreat, full time dwelling or investment opportunity. The land features a mix of mature hardwoods and potential

Morriah Adams BHG Masiello Brattleboro

0 Skyline Dr, Vernon, VT 05354
/29
$285,000
- 4 Beds
- 1 Bath
- 1,466 Sq Ft
625 Plain Rd, Hinsdale, NH 03451

Welcome to 625 Plain Road, a spacious and charming 4-bedroom home set on a beautiful 1.11-acre open lot in scenic Hinsdale, New Hampshire. This property combines comfort, space, and convenience—perfect for anyone looking to enjoy a quiet country setting while staying close to town amenities. Step inside to find a warm and inviting layout with plenty of natural light. The expansive kitchen is

Bob Barnard Monadnock Realty Group LLC

625 Plain Rd, Hinsdale, NH 03451
/51
$544,400
- 6 Beds
- 4 Baths
- 3,000 Sq Ft
22 Chestnut St, Brattleboro, VT 05301

4 condo units being sold together as a great residential package investment opportunity! Rent them, live in one and/or sell them off individually. This offering includes 4 of 5 units in a charming condo development just minutes from downtown, the hospital, shopping, and I-91. Unit 5 has been sold. The property features a large shared yard, off-street parking, and strong rental potential. The

Erica Reynolds Southern Vermont Realty Group

22 Chestnut St, Brattleboro, VT 05301
/5
$315,000
- 3 Beds
- 2.5 Baths
- 2,014 Sq Ft
412 Western Ave, Brattleboro, VT 05301

The cutest house on the block! Only 1 house from the famous deli for eats, right near the entrance to I 91, both north and south for travel or work and 2 minutes away from Memorial Park with all it offers....skating, ball games, pools, sliding, skiing. Plus it has a great back yard, 2 levels of decks and a front porch to add to the package. This 1860's Mansard is so sweet, filled with character

Christine Lewis Brattleboro Area Realty

412 Western Ave, Brattleboro, VT 05301
/12
$425,000
- 3 Beds
- 2 Baths
- 2,074 Sq Ft
36 Spruce St, Brattleboro, VT 05301

New Price! $25,000.00 price drop and a revised offering... If you saw this home before you want to take a second look! The 2nd floor is now vacant! ..and ready for owner occupancy. The basement, barn and lower building are empty and ready for all YOUR stuff. Plenty of undercover storage for boats, special vehicles or lots of other toys. A workshop? Home is just right for 2 family use or

Christine Lewis Brattleboro Area Realty

36 Spruce St, Brattleboro, VT 05301
/5
$89,000
- Land
- 0.21 Acre
- $423,810 per Acre
46-48 Lexington Ave, Brattleboro, VT 05301

This open, level, in-town building lot is a blank slate awaiting its next chapter. Tucked away in a small neighborhood on a dead-end street, this location offers easy accessibility to shopping, restaurants, public transportation and the interstate. Utilities are readily available, including existing hookups for town water and sewer. A unique opportunity!

Stephanie Wilde Brattleboro Area Realty

46-48 Lexington Ave, Brattleboro, VT 05301
/5
$680,000
- Studio
- 5,540 Sq Ft
50 Terrace St, Brattleboro, VT 05301

SUPERB OPPORTUNITY to acquire one of Brattleboro’s nicest multi-family, investment properties!! Situated in one of THE BEST neighborhoods in Brattleboro, Vermont, this sweet, money-maker offers 7 units on a quiet street that is SOOO close to downtown Brattleboro. What every investor dreams of!!! Location, quality condition and build, spacious unit size, superb level, off-street parking, and

Dan Normandeau Berkley & Veller Greenwood Country

50 Terrace St, Brattleboro, VT 05301

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.